Dichloro-substituted imidazole derivatives as antifungal agents

Abstract

Dichloro-substituted 1-(5H-dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole compounds of formula (I), in which -X- is either -CH2-CH2- or -CH=CH-, and their pharmaceutically acceptable addition salts, preferably the nitric acid ones. Products of formula (I) are prepared from products of formula (VI) where Z represents a leaving group such as halogen, by treatment with an excess of imidazole in dimethylformamide. Products (I) show an antifungal activity comparable -or superior- to antimycotics in the market, such as Clotrimazole and Bifonazole. <IMAGE> (I) <IMAGE> (VI)

What is claimed is: 
     
       1. Dichloro-substituted 1-(5H-dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole compound of formula (I), where --X-- is either a --CH 2  --CH 2  -- or a --CH═CH-- group, and pharmaceutically acceptable salts thereof. ##STR9## 
     
     
       2. A pharmaceutical composition for treating fungal infections in humans and animals which comprises an antifungal effective amount of a compound of formula (I) in claim 1 or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable excipient or carrier. 
     
     
       3. Method for treating antifungal infections in humans and animals which comprises administering an antifungal effective amount of a compound of formula (I) in claim 1 or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable excipient or carrier. 
     
     
       4. The compound according to claim 1 wherein --X-- is --CH 2  --CH 2  --, such compound being 1-(2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole, or a pharmaceutical acceptable salt thereof. 
     
     
       5. A pharmaceutical composition for treating fungal infections in humans and animals according to claim 2 which comprises an antifungal effective amount of 1-(2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole or a pharmaceutical acceptable salt thereof in combination with a pharmaceutically acceptable excipient or carrier. 
     
     
       6. Method according to claim 1 which comprises administering an antifungal effective amount of 1-(2,4-dichloro-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl) -1H-imidazole or a pharmaceutical acceptable salt thereof, in combination with a pharmaceutically acceptable excipient or carrier. 
     
     
       7. The compound according to claim 1 wherein --X-- is --CH═CH--, such compound being 1-(2,4-dichloro-5H-dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole, or a pharmaceutical acceptable salt thereof. 
     
     
       8. A pharmaceutical composition for treating fungal infections in humans and animals according to claim 2 which comprises an antifungal effective amount of 1-(2,4-dichloro-5H-dibenzo[a,d]cyclohepten-5-yl)-1H -imidazole or a pharmaceutical acceptable salt thereof in combination with a pharmaceutically acceptable excipient or carrier. 
     
     
       9. Method for treating antifungal infections in humans and animals which comprises administering an antifungal effective amount of 1-(2,4-dichloro-5H-dibenzo[a,d]cyclohepten-5-yl)-1H-imidazole or a pharmaceutical acceptable salt thereof, in combination with a pharmaceutically acceptable excipient or carrier.